CN114729221B - Two-component solvent-borne coating compositions - Google Patents
Two-component solvent-borne coating compositions Download PDFInfo
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- CN114729221B CN114729221B CN202080084099.1A CN202080084099A CN114729221B CN 114729221 B CN114729221 B CN 114729221B CN 202080084099 A CN202080084099 A CN 202080084099A CN 114729221 B CN114729221 B CN 114729221B
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- 239000008199 coating composition Substances 0.000 title claims abstract description 94
- -1 acrylate compound Chemical class 0.000 claims abstract description 70
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 239000003446 ligand Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 14
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 14
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 9
- 239000010941 cobalt Substances 0.000 claims abstract description 7
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 7
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000539 dimer Substances 0.000 claims abstract description 4
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims abstract 2
- 229920000180 alkyd Polymers 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 claims description 4
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 4
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 4
- RLVFFCFUTQINPR-UHFFFAOYSA-N manganese;1,4,7-trimethyl-1,4,7-triazonane Chemical group [Mn].CN1CCN(C)CCN(C)CC1 RLVFFCFUTQINPR-UHFFFAOYSA-N 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001356 alkyl thiols Chemical class 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 14
- 238000003860 storage Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000006120 scratch resistant coating Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- WLDGDTPNAKWAIR-UHFFFAOYSA-N 1,4,7-trimethyl-1,4,7-triazonane Chemical compound CN1CCN(C)CCN(C)CC1 WLDGDTPNAKWAIR-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
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- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
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- 239000004971 Cross linker Substances 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- HSZUHSXXAOWGQY-UHFFFAOYSA-N [2-methyl-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)COC(=O)C=C HSZUHSXXAOWGQY-UHFFFAOYSA-N 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- VDKDFKRKAPXHBH-UHFFFAOYSA-N [3-(2-sulfanylpropanoyloxy)-2,2-bis(2-sulfanylpropanoyloxymethyl)propyl] 2-sulfanylpropanoate Chemical compound CC(S)C(=O)OCC(COC(=O)C(C)S)(COC(=O)C(C)S)COC(=O)C(C)S VDKDFKRKAPXHBH-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- ASJCSAKCMTWGAH-UHFFFAOYSA-N cyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCC1C(O)=O ASJCSAKCMTWGAH-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- YNESSCJHABBEIO-UHFFFAOYSA-N nonadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCCS YNESSCJHABBEIO-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- CCIDWXHLGNEQSL-UHFFFAOYSA-N undecane-1-thiol Chemical compound CCCCCCCCCCCS CCIDWXHLGNEQSL-UHFFFAOYSA-N 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F9/00—Compounds to be used as driers, i.e. siccatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention relates to a two-component solvent-borne coating composition comprising: a comprises a component comprising an autoxidisable resin comprising an unsaturated fatty acid and a metal-ligand complex as a drying catalyst wherein the metal is manganese, vanadium or iron; and B a component comprising a (meth) acrylate compound and a thiol compound, wherein the (meth) acrylate compound is a poly (meth) acryl functional ester of (meth) acrylic acid and a polyol or a poly (meth) acryl functional dimer of such an ester, wherein component B is free of a drying catalyst, wherein component a is free of a thiol group-containing compound and a (meth) acryl functional group-containing compound, wherein the coating composition is free of cobalt.
Description
Technical Field
The present invention relates to two-component solvent-borne coating compositions and to substrates coated with coatings deposited from such coating compositions.
Background
Two-component solvent borne coating compositions that produce very hard scratch-resistant coatings are known in the art. Such coatings are typically based on isocyanate curing technology. Such coating compositions include a resin component, such as an OH-functional polyester or alkyd, comprising a binder polymer having isocyanate-reactive functional groups, and a curing component comprising an isocyanate-functional curing agent, typically a diisocyanate.
However, isocyanate functional curing agents are toxic and constitute a health hazard to the user. Thus, there is a need for isocyanate-free coating compositions that provide coating-like properties.
Coating compositions based on alkyd resins or other autoxidisable resins generally produce coatings which are not as hard or scratch-resistant as isocyanate-crosslinked coatings. To increase the hardness of alkyd-based coatings, alkyd resins have been blended with compounds having either an acryl or methacryl functionality.
For example, in US 4,014,830, a coating composition is disclosed comprising an alkyd resin blended with 1 to 10 wt% of a polyacrylate or polymethacrylate of a polyol based on the total weight of the blend.
In WO 01/46294 a one-component coating composition is disclosed which comprises an alkyd resin, a drier and a polythiol as a crosslinker. The equivalent ratio of SH functional groups to unsaturated carbon-carbon bonds is less than 0.3; in embodiments between 0.04 and 0.12.
In WO 02/46294 polythiols are added to alkyd resins to improve curing at low temperatures compared to conventional alkyd coating compositions.
However, it has been found that the addition of thiol compounds to drier-containing alkyd resins results in limited storage stability and unwanted sulfide odor.
None of the alkyd-based coating compositions disclosed in the prior art produce coatings having hardness comparable to isocyanate-cured coating compositions.
There is a need for improved hard scratch resistant coatings that do not use isocyanate curing.
Summary of The Invention
It has now been found that an isocyanate-free hard scratch-resistant coating can be obtained from a two-component solvent-borne coating composition having component a comprising an autoxidisable resin with unsaturated fatty acids and a metal-ligand complex as a drying catalyst; and component B comprising a (meth) acrylate compound having a poly (meth) acryloyl function and a thiol compound.
Accordingly, the present invention provides in a first aspect a two-component solvent borne coating composition comprising:
a comprises a component comprising an autoxidisable resin comprising an unsaturated fatty acid and a metal-ligand complex as a drying catalyst wherein the metal is manganese, vanadium or iron; and
b a component comprising a (meth) acrylate compound and a thiol compound, wherein the (meth) acrylate compound is a poly (meth) acryl-functional ester of (meth) acrylic acid and a polyol or a poly (meth) acryl-functional dimer of such an ester,
wherein component B is free of dry catalyst,
wherein component A is free of thiol-group-containing compounds and (meth) acryloyl-functional compounds,
wherein the coating composition is free of cobalt.
The coating composition according to the invention has been found to produce a very hard scratch-resistant coating which is tack-free shortly after application.
In addition, components a and B each have been found to be storage stable and the coating composition has an acceptable pot life after mixing the two components. Another advantage of the coating composition according to the invention is that it can be formulated without the unpleasant odours typical of hydrogen sulphide.
In a second aspect, the present invention provides a substrate coated with a coating deposited from a coating composition according to the first aspect of the present invention.
Detailed Description
The coating composition according to the invention is a two-component solvent-borne coating composition. Which comprises component a and component B. The components a and B are manufactured and stored separately and combined shortly before use to obtain the coating composition. Pot life (during which the coating composition can be applied at a temperature of 15 to 25 ℃ without increasing the viscosity to such an extent that reapplication is not possible due to the crosslinking reaction) depends on the ingredients used, in particular the autoxidisable resins, drying catalysts, (meth) acrylate compounds and thiol compounds. Preferably, the pot life of the coating composition is in the range of 30 minutes to 240 minutes, more preferably 60 minutes to 120 minutes.
Component a comprises an autoxidisable resin comprising unsaturated fatty acids. Autoxidisable resins with unsaturated fatty acids are resins which form a film by evaporation of a liquid carrier (organic solvent and/or water) and then harden the resin by free radical autoxidation. The latter is known as chemical or oxidative drying. Unsaturated carbon-carbon bonds in fatty acids react with oxygen from the atmosphere to form hydroperoxides, which then decompose to form free radicals. Recombination of these radicals results in covalent bonds being formed between the polymer chains. In this way, the liquid coating composition comprising the autoxidisable resin hardens to form a solid cured coating. This process is also known as autoxidation or oxidative drying.
The autoxidisable resin in component a may be any suitable autoxidisable resin comprising an unsaturated fatty acid, for example a polyacrylate or alkyd modified with an unsaturated fatty acid, preferably an alkyd.
Preferably, the autoxidisable resin comprises an unsaturated fatty acid having 12 to 22 carbon atoms, more preferably an unsaturated fatty acid having two or more unsaturated carbon-carbon bonds and 12 to 22 carbon atoms. Examples of suitable unsaturated fatty acids include oleic acid, ricinoleic acid, linoleic acid, linolenic acid, and eleostearic acid. Fatty acids derived from linseed oil, sunflower oil, soybean oil, tung oil or canola oil are particularly suitable. The fatty acid contained in the autoxidisable resin preferably has an iodine value in the range 120 to 180, more preferably 135 to 180. Iodine number is defined as the mass of iodine in grams consumed by 100 grams of fatty acid. Reference herein to iodine values is to iodine values determined in accordance with ISO 3961.
In a preferred embodiment, the autoxidisable resin is an alkyd resin.
The alkyd resin may be any suitable alkyd resin. Suitable alkyd resins are known in the art and may be obtained by the reaction of a polyol, a polyacid and an unsaturated oil or fatty acid.
Examples of suitable diols include ethylene glycol, 1, 3-propanediol, 1, 6-hexanediol, 1, 12-dodecanediol, 3-methyl-1, 5-pentanediol, 2, 4-trimethyl-1, 6-hexanediol, 2-dimethyl-1, 3-propanediol, and 2-methyl-2-cyclohexyl-1, 3-propanediol. Examples of suitable triols are glycerol, trimethylolethane and trimethylolpropane. Suitable polyols having more than three hydroxyl groups are pentaerythritol, sorbitol and etherification products of the compounds concerned, such as ditrimethylolpropane and di-, tri-and tetrapentaerythritol.
Examples of suitable polyacids include phthalic acid, citric acid, fumaric acid, mesaconic acid, maleic acid, citraconic acid, isophthalic acid, terephthalic acid, 5-t-butylisophthalic acid, trimellitic acid, pyromellitic acid, succinic acid, adipic acid, 2, 4-trimethyladipic acid, azelaic acid, sebacic acid, dimerized fatty acids, cyclopentane-1, 2-dicarboxylic acid, cyclohexane-1, 2-dicarboxylic acid, 4-methylcyclohexane-1, 2-dicarboxylic acid, tetrahydrophthalic acid, endomethylene-cyclohexane-1, 2-dicarboxylic acid, butane-1, 2,3, 4-tetracarboxylic acid, endoisopropylidene-cyclohexane-1, 2-dicarboxylic acid, cyclohexane-1, 2,4, 5-tetracarboxylic acid, and butane-1, 2,3, 4-tetracarboxylic acid. If desired, the carboxylic acids concerned can be used as anhydrides or in the form of esters, preferably esters of alcohols having 1 to 4 carbon atoms.
The alkyd resin is preferably an alkyd resin having a short oil length, more preferably from 20 to 40%, still more preferably from 25 to 38% oil length. References herein to oil length refer to the weight of fatty acids based on the total solids weight of the alkyd resin.
The alkyd resin preferably has a number average molecular weight in the range of 1,000 to 5,000g/mol, more preferably 1,500 to 3,500g/mol, still more preferably 2,000 to 3,000 g/mol. The weight average molecular weight of the alkyd resin is preferably in the range of 5,000 to 50,000g/mol, more preferably 10,000 to 30,000g/mol, still more preferably 12,000 to 20,000 g/mol. In a particularly preferred embodiment, the alkyd resin has a number average molecular weight in the range of 1,500 to 3,500g/mol and a weight average molecular weight in the range of 10,000 to 30,000 g/mol. Reference herein to weight average molecular weight and number average molecular weight is to weight average molecular weight and number average molecular weight determined by Gel Permeation Chromatography (GPC) using polystyrene standards according to ISO 16014-1.
The dry catalyst in component a is a metal-ligand complex in which the metal is manganese, vanadium or iron. Manganese-, vanadium-, and iron-ligand complexes are known in the art as main driers for autoxidisable resins such as alkyd resins. Any suitable manganese-, vanadium-, or iron-ligand complex may be used, such as bis (acetylacetonate) vanadyl, or a complex of iron or manganese with a nitrogen donor ligand. Preferably, the dry catalyst is an iron-ligand complex or a manganese-ligand complex, as it has been found that coating compositions having an iron-ligand complex or a manganese-ligand complex have a better pot life than coating compositions using a vanadium-ligand complex as the dry catalyst.
Suitable complexes of iron or manganese with nitrogen donor ligands are disclosed, for example, in WO 2012/079624 and WO 2012/093250. Suitable iron-ligand complexes include complexes of iron and Bispidine ligands, particularly iron-Bispidon complexes. More preferably, the dry catalyst is a manganese-ligand complex, even more preferably a manganese-1, 4, 7-trialkyl-1, 4, 7-triazacyclononane complex. Manganese-1, 4, 7-trimethyl-1, 4, 7-triazacyclononane complex is particularly preferred.
The metal and ligand may be added separately to component a to form the metal-ligand complex in situ. If the metal ligand complex is, for example, a manganese-1, 4, 7-trimethyl-1, 4, 7-triazacyclononane complex, manganese may be added as a manganese carboxylate and the ligand may be added as such. Manganese-1, 4, 7-trimethyl-1, 4, 7-triazacyclononane complex is then formed in component A in the same manner as described in WO 2013/092441.
The coating composition is free of cobalt and the resin component is therefore free of cobalt-based drying catalysts. It has been found that the presence of cobalt in a coating composition comprising an autoxidisable resin, (meth) acrylate compound and thiol compound in combination as defined herein results in a red colour change of the coating composition after mixing of the cobalt containing component with the thiol compound containing component.
Component a may further comprise a co-drier (coordination drier) and/or a sub-drier. The co-ordinating drier, also known as a through drier (drier), promotes film formation by interacting with the carboxyl and hydroxyl groups in the polymer base. Thus, the coordinating drier may bridge two or more polymer chains. Such carboxyl and hydroxyl groups may be initially present in the alkyd resin or may be formed during drying. The harmonizing drier comprises a metal drier based on zirconium (Zr), strontium (Sr), aluminum (Al), bismuth (Bi), lanthanum (La), neodymium (Nd), lead (Pb) or barium (Ba). Secondary driers, also known as auxiliary driers, are metal-based compounds which exist in a single oxidation state and are not themselves catalytically active. The secondary drier affects the drying rate by interacting with the primary drier. The secondary drier includes calcium (Ca), zinc (Zn), potassium (K) and lithium (Li) metal soaps.
Component a preferably comprises an antiskinning agent. Antiskinning agents are known in the art and include phenols, hydroquinones, hydroxylamines, particularly N, N-dialkylhydroxylamines, and oximes.
Component B comprises a (meth) acrylate compound and a thiol compound. The (meth) acrylate compound and the thiol compound are preferably different compounds, wherein the (meth) acrylate compound does not contain a thiol functional group and the thiol compound does not contain a (meth) acryl functional group.
The (meth) acrylate compound is a poly (meth) acryl-functional ester of acrylic acid or methacrylic acid and a polyol, or a poly (meth) acryl-functional dimer of such an ester. Such compounds have a relatively low molecular weight and have two or more polymerizable (meth) acryloyl functions, preferably 2 to 4 polymerizable (meth) acryloyl functions. The compounds are therefore preferably di-, tri-or tetra- (meth) acryloyl-functional compounds. Preferably, the molecular weight of the (meth) acrylate compound is in the range of 180 to 500g/mol, more preferably 200 to 400 g/mol.
Examples of suitable (meth) acrylate compounds include trimethylolethane triacrylate, trimethylolpropane triacrylate, trimethylolethane trimethacrylate, trimethylolpropane trimethacrylate, tetramethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1, 3-propanediol dimethacrylate, 1, 4-butanediol dimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and di (trimethylolpropane) tetraacrylate.
Preferably, the (meth) acrylate compound is a methacrylate compound, i.e. an ester of methacrylic acid and a polyol. It has been found that component B containing methacrylate compounds has better storage stability than similar acrylate compounds. Preferred methacrylate compounds are trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, neopentyl glycol dimethacrylate and pentaerythritol tetramethacrylate, more preferably trimethylolpropane trimethacrylate.
The thiol compound may be a monofunctional, difunctional or polyfunctional thiol compound. The thiol compound preferably has a molecular weight in the range of 100 to 10,000g/mol, more preferably 120 to 5,000g/mol, still more preferably 130 to 1,000 g/mol. Preferably, the thiol compound is an alkyl thiol having at least 6 carbon atoms, in particular 10 to 20 carbon atoms, or an ester of thioglycolic acid, 2-mercaptopropionic acid or 3-mercaptopropionic acid with an alcohol or a polyol, such as glycol, pentaerythritol, dipentaerythritol or trimethylolpropane. More preferred thiol compounds are selected from the group consisting of 1-undecanethiol, 1-dodecanethiol, 1-hexadecanethiol, 1-octadecanethiol, 1-nonadecanethiol, ethylene glycol bis (mercaptoacetate), ethylene glycol bis (2-mercaptopropionate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (2-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (mercaptoacetate), pentaerythritol tetrakis (2-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), and mixtures of two or more thereof. Particularly preferred thiol compounds are trifunctional or tetrafunctional thiol compounds, more particularly trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis (3-mercaptopropionate).
The molar ratio of thiol groups in the thiol compound to ethylenically unsaturated groups in the (meth) acrylate compound is preferably in the range of 0.01 to 0.10, more preferably 0.04 to 0.06. It has been found that at higher ratios, the time for the applied coating to become tack-free increases. It was also found that at higher ratios the film properties were poor. If the ratio is extremely low, typically less than 0.01, the tack-free time undesirably increases.
All thiol compounds and all (meth) acrylate compounds in the coating composition are in component B. Component a is therefore free of thiol compounds and free of (meth) acrylate compounds. Component a does not contain any compounds having thiol groups or having (meth) acryloyl functions. Component B does not contain any dry catalyst. Thus, the thiol compound or (meth) acrylate compound is prevented from being present in a single component together with the dry catalyst. It has been found that this brings about an excellent storage stability of the coating composition.
The coating composition (components a and B together) preferably comprises 20 to 40 wt.% of the unsaturated fatty acid-containing autoxidisable resin as specified above. At least a portion of the autoxidisable resin comprising unsaturated fatty acids in the coating composition is in component a. A portion of the autoxidisable resin may be in component B. Preferably at least 50 wt% of the autoxidisable resin is in component a, more preferably at least 80 wt% and even more preferably all of the autoxidisable resin is in component a. Preferably, the coating composition is free of any binder resin other than the autoxidisable resin comprising unsaturated fatty acids.
The amounts of autoxidisable resin and (meth) acrylate compound are preferably such that when the two components are combined to form a coating composition, the coating composition comprises 15 to 40 wt% of (meth) acrylate compound based on the total weight of autoxidisable resin and (meth) acrylate compound.
The composition is a solvent-borne composition. The autoxidisable resin in component a is dissolved in an organic solvent. Component B may be solvent-free or contain an organic solvent to obtain the desired viscosity. Preferably, both components comprise an organic solvent. The total coating composition, i.e. after combining components a and B, preferably has an organic solvent content in the range of 25 to 45 wt%, more preferably 30 to 42 wt%.
Any suitable organic solvent may be used. Suitable organic solvents are known in the art and include aromatic hydrocarbon solvents such as toluene and xylene, aliphatic hydrocarbon solvents such as straight and branched chain paraffins containing from 6 to 10 carbon atoms, and oxygenated organic solvents such as alcohols, glycol ethers, glycol esters, alkyl acetates, ketones, esters, and glycol ethers/esters. An oxygen-containing organic solvent is preferred.
The composition may comprise some water, preferably less than 10 wt%, more preferably less than 5 wt%. Typically, the coating composition comprises 0.5 to 3 wt% water.
The coating composition preferably has a solids content of 55 to 75 wt%, more preferably 58 to 70 wt%. Reference herein to solids content refers to solids content determined according to ISO 3251 with an initial sample mass of 1.0g, a test duration of 60 minutes, at a temperature of 125 ℃.
The coating composition may contain additional ingredients commonly used in coating compositions, such as white and colored pigments, extender pigments and one or more additives, for example, uv stabilizers, dispersants, surfactants, antistatic agents, flame retardants, lubricants, antifoam agents, plasticizers, antifreeze agents, waxes, thickeners, leveling agents and biocides. Pigments and additives may be included in either or both of components a and B. The pigment is preferably contained in component a.
It has been found that the coating composition according to the invention is storage stable, i.e. neither component a nor component B gels upon storage. Furthermore, it has been found that component B does not give rise to an unacceptable degree of sulphide smell. After combining the two components, the coating composition has an acceptable pot life for application to a substrate. The applied coating composition has been found to produce a hard scratch-resistant coating when air dried at ambient conditions. The top-dry coating is obtained in a relatively short time. The curing or top-drying coating can be initiated in a short time without the need to add peroxide or other free radical polymerization initiator to the combined components a and B.
In a final aspect, the invention relates to a substrate coated with a coating deposited from a coating composition according to the invention. The substrate may be any suitable substrate, such as a wood, polymer, composite, metal or mineral substrate. The coating composition may be applied to bare substrates or primed substrates. The coating composition may be applied as a primer or a topcoat, preferably as a topcoat. One or more layers of the coating composition may be applied. If the coating composition is used as a primer, it preferably comprises typical primer components, such as fillers. Preferably, the coating composition is applied as a top coat.
Examples
The invention is further illustrated by the following non-limiting examples.
Preparation of Components A and B
Alkyd resin solution 1
A solution of 80 wt% alkyd resin in xylene was prepared as follows. A mixture of fatty acids derived from soybean oil, phthalic anhydride (300 parts by weight), benzoic acid (338 parts by weight), maleic anhydride (7 parts by weight) and pentaerythritol (308 parts by weight) was reacted in xylene at 230 ℃ until an acid number of less than 10mg KOH/g was obtained. The alkyd resin obtained had an oil content of 35%, a number average molecular weight of 2,663g/mol, a weight average molecular weight of 19,267g/mol and a viscosity of 84Pa.s (with a cone-plate viscometer at 23℃and 100s -1 Measured at shear rate).
Alkyd resin solution 2
A solution of 80 wt% alkyd resin in xylene was prepared as follows. A mixture of fatty acids derived from linseed oil, phthalic anhydride (291 parts by weight), benzoic acid (343 parts by weight), maleic anhydride (7 parts by weight) and pentaerythritol (305 parts by weight) was reacted in xylene at 230 ℃ until an acid value of less than 12mg KOH/g was obtained. The alkyd resin obtained had an oil content of 35%, a number average molecular weight of 2,349 g/mol, a weight average molecular weight of 18,314g/mol and a viscosity of 51Pa.s (with a cone-plate viscometer at 23℃and 100s -1 Measured at shear rate).
The following desiccants and antiskinning agents were used:
mn Nuodex 10 manganese carboxylate
1,4, 7-trimethyl-1, 4, 7-triazacyclononane with ligand (9.5 wt% solution) in D60/dipropylene glycol methyl ether (1.0:0.4)
Durham Nuodex Calcium 10 calcium carboxylate
Duroct
Zirconium 18% carboxylate
Exkin 2 methyl ethyl ketone oxime
Four different components a were prepared by adding a drier and an antiskinning agent to either alkyd resin solution 1 or alkyd resin solution 2.
The amounts (in% by weight) of the different components in components A1 to A4 are given in table 1.
TABLE 1 Components A1 and A2
The different component B is prepared by combining a (meth) acrylate compound and a thiol compound.
TABLE 2 Components B1 to B9
| B1 | B2 | B3 | B4 | B5 | B6 | B7 | B8 | B9 | |
| Trimethylolpropane trimethacrylate | 91 | 87 | 95 | 91 | 100 | ||||
| Trimethylolpropane triacrylate | 91 | ||||||||
| Di (trimethylolpropane) tetraacrylate | 91 | 95 | |||||||
| Trimethylol propane tris (3-mercaptopropionate) | 9 | 9 | 9 | 5 | 5 | 100 | |||
| 1-dodecanethiol | 13 | 9 |
Test method
The coating film was evaluated using a pendulum damping test according to ISO 1522:2006
Hardness. A glass plate was coated with a 150 μm wet film, kept at 21℃and 49% relative humidity and treated with +.>
The pendulum monitors the development of hardness in time. The number of oscillations required to reduce the deflection from an initial deflection of 6 ° to a deflection of 3 ° was measured. The average of two replicates was recorded. Measuring +.A.A.after 1 day, 8 days, 14 days, 4 weeks, 8 weeks and/or 3 months storage at 21℃and 49% relative humidity +.>
Hardness.
Time of surface drying
A wet layer of the coating composition was applied on a glass plate (10X 30 cm) using a K-control coater with a bar applicator (gap size 150 μm). The coated glass sheet was allowed to dry at 22 ℃ and 44% relative humidity on a table. A small cotton ball was dropped onto the plate from a height of 10-15 cm at regular time intervals after application. The plate is then immediately lifted at one of its short sides while the other short side is still resting on the table and rotated to a vertical position (at an angle of 90 deg. to the table). If the batting is adhered to the panel, the coating is not tack-free. The time that the cotton ball falls off the plate is the time that the coating is considered to be dry.
Examples1–Hardness and open time
Coating compositions (component amounts in parts by weight) were prepared by manually mixing component a and component B as shown in tables 3 and 4. Watch (watch)Coating compositions 2 to 8 in 3 and coating compositions 13 to 17 in table 4 are coatings according to the invention; coating compositions 1 and 9 to 11 in table 3 and coating compositions 12 and 18 to 20 in table 4 are comparative compositions (indicated by x). Determination as described above
Hardness and tack-free time. The results are shown in tables 3 and 4. The results show that the coating composition according to the invention forms an acceptable hardness and has an acceptable open time.
TABLE 3 coating compositions 1 to 11
TABLE 4 coating compositions 12 to 20
a Use of a rotational viscometer at 23℃and 10,000s -1 Is measured at the shear rate of (2)
b The number of oscillations required to reduce the initial deflection from 6 to 3
EXAMPLE 2 storage stability
Different two-part coating compositions were prepared, all having similar overall compositions (if the respective components A and B were combined in a 2:1 weight ratio). Composition 21 is a composition according to the invention. Compositions 22 to 25 are comparative compositions.
The storage stability of components a and B was determined by storing the components at 50 ℃ and visually and olfactively inspecting the components after 4 weeks.
The ingredients (in weight%) and the storage stability of the different components a and B of the respective coating compositions 21 to 25 are given in table 4. Components A23 and A24 gel. In addition, component a24 gives rise to a strong sulfide odor. Components A21, A22 and A25 were storage stable (no gelation; no sulfide odor generation). Components B22 and B25 gel. Components B21, B23 and B24 are storage-stable (no gelling; no sulfide odor generation).
Coating composition 21 (according to the present invention) is the only coating composition (no gelation of any of the components) whose two components can be combined to form the coating composition.
TABLE 4 coating compositions 21 to 25 composition (wt%) and storage stability
c Pentaerythritol tetrakis (3-mercaptopropionate)
d Trimethylolpropane trimethacrylate
Claims (22)
1. A two-part solvent borne coating composition comprising:
a comprises a component comprising an autoxidisable resin comprising an unsaturated fatty acid and a metal-ligand complex as a drying catalyst wherein the metal is manganese, vanadium or iron; and
b a component comprising a (meth) acrylate compound and a thiol compound, wherein the (meth) acrylate compound is a poly (meth) acryl-functional ester of (meth) acrylic acid and a polyol or a poly (meth) acryl-functional dimer of such an ester,
wherein component B is free of dry catalyst,
Wherein component A is free of thiol-group-containing compounds and (meth) acryloyl-functional compounds,
wherein the coating composition is free of cobalt.
2. The two-component solvent-borne coating composition according to claim 1, wherein the molar ratio of thiol groups in the thiol compound to ethylenically unsaturated groups in the (meth) acrylate compound is in the range of 0.01 to 0.10.
3. The two-component solvent-borne coating composition according to claim 2, wherein the molar ratio of thiol groups in the thiol compound to ethylenically unsaturated groups in the (meth) acrylate compound is in the range of 0.04 to 0.06.
4. A two-component solvent-borne coating composition according to claim 1 or 2, wherein the coating composition comprises 15 to 40 wt.% of the (meth) acrylate compound based on the total weight of the autoxidisable resin and the (meth) acrylate compound.
5. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the solids content of the coating composition is in the range of 55 to 75% by weight.
6. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the (meth) acrylate compound is a di-, tri-or tetra- (meth) acryloyl functional compound.
7. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the (meth) acrylate compound is a methacrylate compound.
8. The two-part solvent-borne coating composition according to claim 7, wherein the (meth) acrylate compound is trimethylolpropane trimethacrylate.
9. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the fatty acid contained in the autoxidisable resin has an iodine value in the range 135 to 180.
10. A two-component solvent borne coating composition according to any one of the preceding claims wherein the autoxidisable resin is an alkyd resin.
11. The two-part solvent borne coating composition according to claim 10, wherein the alkyd resin has a weight average molecular weight in the range of 10,000 to 30,000 g/mol.
12. The two-part solvent borne coating composition according to claim 11, wherein the alkyd resin has a weight average molecular weight in the range of 12,000 to 20,000 g/mol.
13. A two-component solvent borne coating composition according to claim 10 or 11, wherein the alkyd resin has a number average molecular weight in the range 1,500 to 3,500 g/mol.
14. The two-part solvent borne coating composition according to claim 13, wherein the alkyd resin has a number average molecular weight in the range of 2,000 to 3,000 g/mol.
15. A two-part solvent borne coating composition according to any one of claims 10 to 13 wherein the alkyd resin has an oil length of from 20 to 40%.
16. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the dry catalyst is an iron-ligand complex or a manganese-ligand complex.
17. A two-part solvent borne coating composition according to claim 16 wherein the dry catalyst is a manganese-ligand complex.
18. The two-part solvent borne coating composition according to claim 17, wherein the drying catalyst is a manganese-1, 4, 7-trimethyl-1, 4, 7-triazacyclononane complex.
19. A two-component solvent borne coating composition according to any one of the preceding claims, wherein the thiol compound is an alkyl thiol having from 10 to 20 carbon atoms, or an ester of thioglycolic acid, 2-mercaptopropionic acid or 3-mercaptopropionic acid with a diol, pentaerythritol, dipentaerythritol or trimethylolpropane.
20. A two-part solvent borne coating composition according to claim 19 wherein the thiol compound is a trifunctional or tetrafunctional thiol compound.
21. A two-component solvent-borne coating composition according to claim 20, wherein the thiol compound is trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis (3-mercaptopropionate).
22. A substrate coated with a coating deposited from a coating composition according to any one of the preceding claims.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19214856 | 2019-12-10 | ||
| EP19214856.7 | 2019-12-10 | ||
| PCT/EP2020/084848 WO2021116006A1 (en) | 2019-12-10 | 2020-12-07 | Two-component solvent-based coating composition |
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| CN114729221A CN114729221A (en) | 2022-07-08 |
| CN114729221B true CN114729221B (en) | 2023-05-12 |
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| CN202080084099.1A Active CN114729221B (en) | 2019-12-10 | 2020-12-07 | Two-component solvent-borne coating compositions |
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| US (1) | US20230053381A1 (en) |
| EP (1) | EP4073183B1 (en) |
| CN (1) | CN114729221B (en) |
| AU (1) | AU2020402084A1 (en) |
| ES (1) | ES2969367T3 (en) |
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| EP4414430A1 (en) * | 2023-02-09 | 2024-08-14 | PPG Europe B.V. | Drier and anti-skinning agent system for a coating composition |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4014830A (en) | 1975-10-30 | 1977-03-29 | Celanese Coatings & Specialties Company | Acrylate or methacrylate modified alkyd resins and epoxy esters |
| ATE148146T1 (en) * | 1990-12-21 | 1997-02-15 | Rohm & Haas | AIR CURING POLYMER COMPOSITION |
| GB9824932D0 (en) * | 1998-11-16 | 1999-01-06 | Ici Ltd | Coating composition |
| ATE262002T1 (en) | 1999-12-22 | 2004-04-15 | Akzo Nobel Nv | COATING COMPOSITION CONTAINING AN OXIDATIVE DRYING POLY UNSATURATED CONDENSATION PRODUCT, A POLYTHIOL AND A DESICING AGENT |
| WO2002046294A1 (en) | 2000-12-08 | 2002-06-13 | Atc Dr. Mann E.K. | Method for producing dimensionally stable, spherical carbohydrate particles and the use thereof |
| US7256226B2 (en) * | 2004-03-15 | 2007-08-14 | Hexion Specialty Chemicals, Inc. | Storage-stable acrylate-functional alkyd resin compositions |
| DK2652025T3 (en) | 2010-12-15 | 2018-11-12 | Ppg Europe B V | Dry composition and use thereof |
| EP2474578A1 (en) | 2011-01-06 | 2012-07-11 | Rahu Catalytics Limited | Antiskinning compositions |
| US9540538B2 (en) * | 2011-06-01 | 2017-01-10 | Synres B.V. | Drier for alkyd resin compositions |
| EP2607434A1 (en) | 2011-12-20 | 2013-06-26 | Akzo Nobel Coatings International B.V. | Drier for auto-oxidisable coating composition |
| EP3037464A1 (en) * | 2014-12-24 | 2016-06-29 | Akzo Nobel Coatings International B.V. | Coating composition comprising an alkyd-comprising resin and a drier |
| CN110540795B (en) * | 2018-05-28 | 2021-10-15 | 广东华润涂料有限公司 | Non-isocyanate-curable solvent-borne two-component coating composition |
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| CN114729221A (en) | 2022-07-08 |
| EP4073183B1 (en) | 2023-12-06 |
| AU2020402084A1 (en) | 2022-06-02 |
| US20230053381A1 (en) | 2023-02-23 |
| PL4073183T3 (en) | 2024-06-03 |
| ES2969367T3 (en) | 2024-05-17 |
| EP4073183C0 (en) | 2023-12-06 |
| EP4073183A1 (en) | 2022-10-19 |
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